


On A Roll

by Thirst4Chicken



Category: Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Black & White | Pokemon Black and White Versions
Genre: Age Difference, Anal Sex, Battle Subway (Pokemon), Consensual Underage Sex, Don't Examine This Too Closely, F/M, Isshu-chihou | Unova Region (Pokemon), Older Man/Younger Woman, Oral Sex, Plot What Plot/Porn Without Plot, Pokemon Training, Porn, Semi-Public Sex, Sex for Favors, Shameless Smut, Train Sex
Language: English
Status: Completed
Published: 2020-09-23
Updated: 2020-09-23
Packaged: 2021-03-07 23:48:17
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 6,398
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26616217
Author URL: https://archiveofourown.org/users/Thirst4Chicken/pseuds/Thirst4Chicken
Summary: Hilda 'persuades' a Depot Agent to let her continue with her challenge after suffering defeat in the Battle Subway
Relationships: Touko | Hilda/Depot Agent, Touko | Hilda/Original Male Character(s)
Kudos: 41





	On A Roll

“No way,” Hilda said, her eyes widening even as her last Pokémon automatically returned to its respective Pokeball. “No, no, no! You’ve got to be kidding me!”

The teenage girl was standing on one end of the railway car, facing her opponent as he stood on the other. Sweat glistened on her skin from the effort of battle, dampening her bare legs and arms, largely exposed as they were by her somewhat minimalist outfit, and even her brown hair felt damp, with her ponytail bursting out of the back of her baseball cap. The subway rumbled on around them, its speed undeterred by the ferocious battle which had just taken place within the cab. Such was the way of the Battle Subway; high-intensity battles at even higher speeds!

Not that Hilda noticed any of this. She was much more focused on the fact that, despite her best effort, and the hard work of her Pokémon, she had lost the battle.

Again.

“Sorry, but it’s no joke,” the Depot Agent responded as he confidently withdrew his own Pokémon, holding out the Pokeball until his partner disappeared within. The man appeared to be in his thirties or forties, well-dressed in his crisp green uniform and a kind smile on his face as he appraised the girl he had just defeated in a Pokémon Battle. “You know the rules, your streak ends here. Better luck next time, eh?”

To say Hilda was distraught would be an understatement. Though not yet the Champion of the Unova League as she dreamed to be, she was nonetheless one of the region’s rising Pokémon Trainers, and for good reason. Ever since setting out from Nuvema Town alongside Cheren and Bianca all those months ago, Hilda had done nothing but train and catch Pokémon in her quest to become the very best. She had defeated every opponent in her path, earned Gym Badge after Gym Badge, and even sent Team Plasma packing more than once.

And yet, here she was, on the Battle Subway, losing to a Depot Agent.

_Again_.

“Why can’t I beat you?” Hilda wondered out loud, literally fighting back tears as the realization settled in that she had once again lost her Battle Subway challenge. Even her knees felt wobbly, as though she could barely remain standing. “It doesn’t make any sense!”

“To be fair, we _have_ battled almost a dozen times now,” the Depot Agent pointed out good-naturedly, clearly trying to help the girl. “In fact, I’m pretty sure we’ve fought every day for almost two weeks now. Why do you keep coming back, anyway?”

“Because I have to beat Cheren!”

The Depot Agent blinked. “Cheren?”

“Cheren is my rival,” Hilda began to explain, doing her best to do so without letting her frustration show despite the rapid beating of her heart and her general agitation. “We grew up in Nuvema Town together and now we’re both Pokémon Trainers, but he’s really good at the Battle Subway. Like, _really_ good. So good that he’s been bragging nonstop about _how_ good he is, and the only way to get him to shut up about it is to break his record once and for all!”

“So, you’re just trying to outdo your friend?” the Depot Agent said, raising an eyebrow as he did so. “What’s his record, anyway?”

“Forty straight wins,” Hilda admitted, practically kicking at the floor beneath her even as the subway rumbled on around them. “But I never manage to get past _you_ , no matter what order you are! And today, I’m on a roll. I’m at thirty-eight straight wins. _You_ were supposed to be number thirty-nine!”

“Ouch,” the Depot Agent responded sympathetically, wincing a little. “But, I mean, there’s always tomorrow, right?”

“No, you don’t get it!” Hilda protested, still as frustrated as ever. “I’ve never gotten this close before! And I’ve been doing this for weeks! All I need to do is get past you, and then I’m _sure_ I can beat Cheren’s record. I _know_ I can!”

That part, at least, the Depot Agent believed. In his many fights with Hilda, he had been able to detect just how good of a Trainer she was. In fact, the only reason he managed to beat her each time was largely thanks to type advantages and a few strokes of luck. Despite her adolescence and enthusiasm, Hilda was a force to be reckoned with, and the Depot Agent had grown to look forward to battling the spunky young woman in the baseball cap and short-shorts.

Unfortunately, that didn’t mean he could show her any mercy.

“Well, sorry, but there really isn’t anything I can do,” the Depot Agent said after a moment’s consideration, genuinely wishing he could help despite knowing he couldn’t. “It’s not like I can just lie and let you go on to the next car. I’m a Depot Agent, after all, I report directly to the Subway Bosses. If they found out I let you cheat, I could lose my job!”

Hilda’s heart sank upon hearing the Depot Agent’s words, but a glimmer of hope still remained. Despite everything, it had not gone unnoticed by the teenager that the Depot Agent had been checking her out both before and during their battles over the last week or two. This didn’t bother Hilda any – she was used to guys ogling at her, and sometimes even appreciated the attention – but it did occur to her that it was something she could use to her advantage.

Besides, she really was _so close_! What harm could it do…?

“But…but…but there must be _something_ I can do to convince you!” Hilda exclaimed, tears now glistening at the edges of her eyes as she practically begged the Depot Agent. “Please! I’m so close! I’m so, so, so, so, so _close_!”

“Look, I’m sorry – ”

The Depot Agent didn’t even have the time to finish apologizing before Hilda was literally on her knees in front of him, her mostly bare legs folded and her hands clasped together as she begged for mercy. She looked up at him with her big blue eyes, gleaming with tears as they were, her lip quivering and her hands shaking.

“Please! Please! I’ll do anything! _Anything_!” Hilda pleaded, looking up at the flabbergasted Depot Agent as desperately and as innocently as she knew how, milking the moment for all it was worth. It’s true she was frustrated, frustrated enough even to debase herself in such a manner, but didn’t mean she didn’t know how to use her looks to her advantage. “I’m so close! Just let me past! I won’t tell anyone! Come on, I’m begging you! I’m literally _on my knees_ here!”

The Depot Agent honestly didn’t know how to respond. He had dealt with some sore losers before, and more than his share of crying girls, but he had never had a defeated Trainer literally on their knees before him and begging for him to bend the rules. Particularly never such an attractive Trainer…

Such thoughts proved dangerous. All it took was a single consideration before the older man’s mind began shuffling through anything and everything he had noticed about Hilda, every action she had made, every part of her body he longed to see, to touch to feel…

He thought of Hilda’s long, bare legs, exposed as they were by her ridiculously tiny shorts, so short even the pockets were sticking out, leaving almost nothing to the imagination…

He thought of Hilda’s perky B-cup breasts, covered as they were by her white top, how they moved and bounced beautifully with every movement she made…

He thought of Hilda’s curvy hips and beautifully round ass, perfectly tight and barely restrained by her shorts, just begging to be smacked and groped and worshipped…

Most of all, though, he thought of Hilda’s gorgeous face, youthful and bright, with her big blue eyes and wild brown hair, the confident smirk she always had when she entered the car, ready to battle, her eyes gleaming with enthusiasm and adventure…

All of this occurred to the Depot Agent as he stood there awkwardly in the subway with Hilda kneeling in front of him with her hands clasped in prayer and tears in her eyes. The subway rumbled on around them, neither slowing nor stopping, causing the car to rattle lightly back and forth, a constant reminder to both Hilda and the older man that their time was limited. And, unfortunately, just as the Depot Agent could not stop what thoughts crossed his mind, nor could he control how his body reacted to such thoughts.

Hilda was just about to open her mouth and start begging again when she noticed the movement in the Depot Agent’s pants. She was a little surprised at first, her eyes widening as she noticed the increasingly large and visible bulge taking shape in the older man’s pants, but she quickly took control of the situation. It wasn’t long before the tears in the girl’s eyes were fading away and her pout was slowly shifting into a smile.

This may not have been what Hilda had been expecting…but it was definitely something she could work with!

“Are you _sure_ there isn’t anything I can do to convince you to let me past?” Hilda asked innocently, biting her lip and blushing a little as she looked up at the Depot Agent standing before her. “There’s really _nothing_ a cute girl like me can’t give you?”

“I…I, um…” the Depot Agent stuttered, feeling his face growing red with heat. His erection was clearly visible now, even through is crisp green pants, and he knew Hilda was looking right at it, even if she wasn’t saying so directly. “It’s…that is…t-the rules say…”

“Rules, rules, rules,” Hilda replied, giggling a little and shuffling closer towards the older man. No longer begging, she lifted her hands up and began slowly but expertly undoing the man’s belt, knowing there was nothing he could do to stop her. “Don’t you ever want to break the rules? Just once? Just to see what it feels like…?”

A minute later, the Depot Man’s belt was undone and Hilda was reaching into his pants. Frozen in place and unsure of what to do – if, indeed, he should do anything at all – the Depot Agent could do nothing but gasp as he felt the teenager wrap her soft fingers around his hardening cock and then pull it out so she could take a good look at it.

“Mmmm, so big…” Hilda hummed, still blushing despite herself even as she looked upon the Depot Agent’s fat cock and began stroking it up and down. While it’s true she was trying to get him excited, it didn’t mean she was lying – the Depot Agent was indeed well-endowed, both thick and long, and Hilda was already getting a little excited just looking at his girth. “So big and so hard. I bet I could help with that, if you wanted…”

With that, Hilda began slowly stroking the man’s cock up and down with both hands, moving all the way up and down his hardened shaft and eliciting a clear and unmistakable groan from the Depot Agent. The man even went so far as to close his eyes as he felt the teenager began to gently jack him off, as though she wanted nothing more than to feel his cock.

Hilda went slow at first, as she had learned to do from her few previous sexual experiences – including with Cheren, she noted with a hint of amusement – but she didn’t stay that way for long. She quickened her speed after a while, and soon felt a shiver of pleasure run down her spine when the Depot Agent began responding with gentle moans and groans.

“You like that…?” she asked the older man, looking up at him with her big, blue innocent eyes, even as she passionately stroked his cock.

“Uh-huh…” the Depot Agent groaned, moving his hips slightly in time with the teenager’s masterful strokes.

“Good,” Hilda responded, smiling up at the Depot Agent enthusiastically and licking her lips for what came next. “Then I know you’ll _love_ this…”

A moment later, the Depot Agent felt his eyes shoot wide open and a loud groan burst unsolicited from his mouth as Hilda wrapped her adolescent lips around his fat cock. A shiver of fiery pleasure ran up and down the uniformed man’s spine the moment he felt the girl’s mouth around his cock, and a second one almost brought him to his knees when he soon felt her lovely tongue running up and down his length.

It took everything the Depot Agent had to look down at the beautiful young woman sucking his dick without exploding into her mouth right then and there. The sight of such a gorgeous girl – so young, so enthusiastic, so confident – kneeling in front of him and slowly licking up and down his meaty shaft was almost too much for him to take. A man could only believe in so much!

Hilda, meanwhile, was already hard at work seeing to it the Depot Agent was having the time of his life. Closing her eyes so she could focus, she licked up and down the older man’s cock until it was entirely coated in her saliva. Satisfied, she took it into her mouth again and again, lovingly sucking on the top half of the dick, paying special attention to the head, where she could already taste pre-cum, while using her hand to stroke whatever she couldn’t fit in her mouth. It had been a while since last she gave someone a blowjob – perhaps too long – and she found herself enjoying it almost as much as the Depot Agent on the receiving end.

“Mmmm,” Hilda moaned gently as she began bobbing her head back and forth on the uniformed man’s fat cock, sucking him in a little deeper each and every time he pushed past her inviting lips. Her stroking was becoming faster too as she fought to stuff as much of the Depot Agent’s dick into her mouth as possible, as though she suddenly had an insatiable desire to feel him buried in her throat. “Mmmmm…!”

“Sweet Arceus…!” the Depot Agent groaned above her, fighting just to keep going as he felt the teenager make sweet love to him with her mouth, rolling her tongue around his shaft and sucking him both harder and deeper. Opening his eyes, he looked down at Hilda, as if reminding himself this entire experience was really happening, only for her to look right back up at him and gift him with a playful wink.

The man almost came right then and there.

Miraculously, however, he hung on, and it wasn’t long before the Depot Agent was running his hand through Hilda’s wild brown hair and holding the back of her head as he thrust gently but quickly into her warm and inviting mouth. Hilda, of course, took it like the Champion she knew she would become, only moaning louder and more passionately as she bobbed her head back and forth, back and forth, back forth, stroking whatever she couldn’t fit in her mouth.

Despite everything, Hilda was enjoying herself, and she made this known not only through her happy moans and hums of adoration, but through her desire to seemingly stuff as much of the Depot Agent’s cock into her mouth as she physically could. The head of the man’s dick was already pushing into the back of the teenager’s throat, and she had to concentrate to fight back her gag reflex as she felt it go deeper and deeper still. He was thrusting into her harder and faster now as well, almost fucking her mouth, and Hilda found herself falling more and more in love with the sensation of being used in such a dominant way.

But Hilda wasn’t here just to have a good time, after all. She had a goal in mind, and she hadn’t forgotten, even if the Depot Agent apparently had.

Just as the man in the green suit felt himself reaching his peak, his hand tightening on the back of Hilda’s head and his cock slamming into the back of her throat again and again…Hilda stopped.

“Wha…what?”

The Depot Agent seemed confused, even bewildered, as he felt Hilda pry her lips off his cock and lean back, withdrawing his dick from her mouth with an audible ‘pop’ for the first time since she began the festivities. His cock was throbbing, practically sore with anticipation, and he wanted nothing more than to shove it right back into the teenager’s mouth and explode right down her throat.

“Ah, ah, ah, not so fast,” Hilda suddenly said, as though sensing the Depot Agent’s frustration. She continued to stroke his cock up and down as she spoke, a devilish smile on her face as she looked up at the man she was clearly taking advantage of. “I don’t know what kind of girl you think I am, but I don’t just go around doing this for anyone, you know.”

“You…you mean…the challenge?” the Depot Agent asked, blinking wildly. The man acted as though he was emerging from a trance, as though he had completely forgotten where he was and what was going on.

Hilda smirked; she tended to have that effect on men.

“Fair is fair, right?” Hilda asked innocently, smiling up at the older man as she continued to playfully but rhythmically stroke his cock. “Nobody has to know but us. All you have to do is let me pass so I can kick more butt and beat my friend’s record.”

“And…in return?” the Depot Agent asked uncertainly.

Hilda’s answer came in the form of a playful wink as, still looking up at the man standing before her, she leaned in again and took only the head of his cock into her mouth, sucking passionately until she heard him groan.

“Oh, you know,” she said a moment later after pulling him out of her mouth. “I’m sure you can use your imagination…”

About that, Hilda was quite correct. If the Depot Agent had anything right then and there, it was a very vibrant, very _lively_ imagination.

“Okay, you have a deal,” the Depot Agent said after a brief moment’s consideration, all thought of his job suddenly disappearing in the face of an opportunity to make all his dreams come true in the form of a beautiful teenage girl. “But I want more than just your mouth.”

_Jackpot_ , Hilda thought to herself.

“Yeah?” she asked, smiling confidently as she continued to stroke him gently, wriggling her hips a little even as she remained sitting. “What did you have in mind?”

“Your ass,” the Depot Agent told her breathlessly, as though he had been holding in such a request since the first time he saw her. “I can’t stop thinking about your ass in those tight little shorts of yours. It’s like you’re teasing me. I need it.”

Hilda hesitated. While she had fully expected the Depot Agent to let her get away with just sucking his dick, she knew full-blown sex had been a possibility, and she wasn’t adverse to it. On the contrary, the long she had pleasured the uniformed man, the wetter she had become, and part of her almost hoped he would ask to go the way so she could feel his fat cock buried inside her tight, little pussy.

She had most certainly _not_ anticipated anal.

Not that the girl was very surprised. She knew she had the ass of a goddess, had heard countless boys and men tell her such a thing, and it was part of the reason she wore such tiny shorts in the first place. She liked having a nice ass, liked to flaunt it, and liked the attention it brought her. But was she really going to let this man – this _older_ man, this complete _stranger_ – fuck her ass right here on the subway?

If it meant continuing her challenge and getting Cheren to show up, Hilda was prepared to do anything.

“You want to fuck my ass, huh?” Hilda finally asked coyly, biting her lip and blushing as she looked up at the Depot Agent standing before her. “Then I guess today is your lucky day…”

With that, Hilda pushed herself back up onto her feet, letting go of the Depot Agent’s cock for the first time since she pulled it out of his pants. Giving him another wink, the teenager turned and walked over to the nearest seat, swaying her hips all the while, knowing how much it had to be driving the older man crazy. Then, stopping in front of the seat, Hilda unzipped her shorts and took hold of both them and her panties.

A moment later, Hilda’s shorts and underwear were down by her feet and her bare ass was naked and fully exposed to the world, its beauty earning a gasp from the Depot Agent as he looked upon it for the very first time. The young woman truly had the ass of a goddess, perky and soft and perfectly round, just begging for abuse.

“Well, you gonna stand there staring like a Watchog?” Hilda asked, breaking the man’s concentration as she reached up and took hold of the grab handles swinging from the handrail above her so she could better prop herself up with her back arched and her rear fully presented. “Or are you gonna show me a good time?”

The Depot Agent didn’t have to be asked twice. The older man was upon Hilda mere seconds later, standing right behind her with his hands on her bare ass and his cock hard and ready. He groped and squeezed the teenager’s ample buttcheeks, relishing in the sensation of her perfect flesh in his hands before prying them apart to reveal her puckered, little asshole.

“Hmmm, that’s nice…” Hilda said with a smile, closing her eyes a little and wriggling her butt as she felt the Depot Agent molest it lovingly and with a great deal of care. He wasn’t even inside her yet, and she was already enjoying yourself! “You’ve been wanting to do this for a while, haven’t you?”

“Since the moment I first saw you,” the Depot Agent admitted shamelessly, massaging the girl’s perfect ass even as he prepared to penetrate her, the sensation of which clearly sent a shiver of pleasure running down Hilda’s spine. “It’s like a wish come true…”

Hilda gasped when she first felt the head of the Depot Agent’s cock pressing against her anus, her eyes actually shooting open a little as she faced away from her lover and prepared for what came next. Biting her lip and forcing her eyes closed, the girl did her best to fight back a groan of pain as she then felt the older man give a great push, just enough that the head of his cock was able to slide inside of her. It was all she could do to keep herself breathing as she felt a cockhead buried inside her ass, even knowing more was still to come. Much more.

Truth be told, Hilda had never had anal sex before, and that was one of the reasons (perhaps the primary reason) she had been hesitant to agree to the Depot Agent’s proposal at first, despite how badly she clearly wanted to continue on with her Battle Subway challenge. The girl’s few sexual experiences up to this point had been relatively tame, if enjoyable, and none of them had involved a cock in her butt. This was her first time, her maiden voyage, and she didn’t really know what to expect, but she assumed pain would no doubt be a part of it.

She had been right.

Nonetheless, as the Depot Agent began pushing the rest of his cock into Hilda’s virgin ass, sinking inch after inch of his thick meat inside of her bowels, Hilda found the sensation of being stuffed full from behind was almost outweighing the searing pain shot through her body each time the man pushed a little more of his dick inside her. Having never been anally penetrated before, Hilda was pleasantly surprised to find it felt much like a cock in her cunt, only hotter, tighter, and as though the cock was three times as big.

As such, Hilda did her best to focus on the sensation of being completely and utterly stuffed, relying on that to help her cope with the pain that came with a cock being pushed into her ass for the very first time. By the time the Depot Agent had managed to fit the majority of his dick inside her and began thrusting in and out of her asshole, Hilda was already adapting, bucking her hips to meet the man thrust for thrust even as she swung from the grab handles above.

“Nn! Nn! Nn! Huh! Ughnnn!!” Hilda moaned and whimpered as she felt the Depot Agent begin fucking her ass in earnest, pushing and pulling his cock in and out of her previously virgin anus, each time going a little deeper and just a little harder. The girl closed her eyes and gasped as she felt each thrust send a surge of both pain and pleasure crashing through her body, driving her insane with need. “Huh, huh, huh! Nnnggh!! Oh, fuck, yes…!”

Whether the Depot Agent knew Hilda had been an anal virgin before he penetrated her or not didn’t much matter, since he was quite clearly in heaven. The older man had been fighting not to burst the moment his cock first pressed against Hilda’s beautiful butthole, and it had only grown more and more difficult the deeper he buried himself in Hilda’s impossibly tight bowels, so tight it almost hurt, though it hurt in the absolute best way possible. As far as the Depot Agent was concerned, he didn’t know which was better: the sight of Hilda holding onto the hanging handle for dear life as he slowly but passionately fucked her ass, or the sensation of her adolescent buttcheeks resting against his hips every time he buried himself to the hilt inside her.

“So tight…!” the man gasped as he pushed and pulled his cock in and out of Hilda’s naked ass, loosening her up a little more with every thrust and no doubt stretching her insides like no one ever had before. “Huh! Fuck! This is perfect…!”

And, despite the pain she was experiencing and the situation she found herself in, Hilda found herself agreeing with the Depot Agent’s assessment: it really was perfect!

As the man loosened her up with every thrust and began sliding in and out of her with both more power and more speed, Hilda quickly found the pain she felt being eclipsed by a rising sense of pleasure. The sensation of being so completely and utterly dominated, swinging from handles on a subway as a stranger forced himself into her ass again and again and again, was downright exhilarating, and it wasn’t long before she found herself looking forward to each and every one of the Depot Agent’s brutal thrusts into her tight, adolescent ass.

“Oh, yes, yes, yes, yes, _yessss_!!” Hilda cried out as she bucked her naked hips back towards the Depot Agent with every thrust, a new moan or shout of ecstasy bursting from her mouth every time she felt him take the plunge into her ass. The sound of the man’s hips smacking into her ass every time he buried himself inside her was like music to Hilda’s ears, and she longed to listen to it for as long as she could. “Uhn! Uhn! Uhn! Fuck! Yeah! Just like that…!”

Meanwhile, the Depot Agent was likewise having the time of his life, thrusting faster and harder now that he had managed to loosen Hilda enough. She was still remarkably tight, almost impossibly so, but he reveled in it, even gasping and groaning as she felt her bowels squeezing around his thrusting cock as though trying to milk the cum and ecstasy right out of him. He, too, loved the sound of his hips smacking against Hilda’s naked buttcheeks every time he slammed into her, burying himself to the hilt, so deep it felt like the very life was being squeezed out of him, albeit in the most delicious way possible.

Even more attractive to the man than the sensation of pounding Hilda’s perfect ass was how passionately and enthusiastically she responded. She bucked her hips against him as best she could, her back arching with every thrust, and whimpers and moans bursting unbidden out of her mouth the harder and faster he went. The girl gripped the handles above her tightly, as though hanging on for dear life, her bare legs shaking as she took the Depot Agent’s cock deeper and deeper into warm and wonderful insides. As much as the older man was enjoying himself, it was clear Hilda was, too, and that only made the experience all the better.

The Depot Agent had been with his fair share of women, but nothing – and nobody – measured up to this young, excitable spitfire!

“Mmmm, yeah, fuck me, fuck me, fuck my tight little ass!” Hilda moaned and groaned loudly, her eyes closing and rolling back into her head as she experienced both pain and pleasure she had never before imagined. Every thrust into her ass sent a jolt of ecstasy crashing over her young body, pushing her ever closer to the brink. “Whatever you do, please don’t stop! Just keep fucking my ass! Uhnn! Oh! Oh, it hurts, it hurts, but it hurts _so good_ …!”

Hilda’s loud and passionate moaning only encouraged the Depot Agent to pick up the pace, slamming his cock deeper and deeper into the teenager’s rectum as he gripped her tightly by the hips, anchoring her as he drove himself into her again and again and again. Hilda responded by bucking wildly, screaming and moaning, her ass only growing tighter and tighter the harder and faster she felt the man’s cock drilling into her.

“Damn it, so perfect…!” the Depot Agent groaned loudly as he tightened his grip on Hilda’s bare waist and hammered himself into her harder, faster, and deeper. Every one of the girl’s movements was driving him crazy, pushing him over the edge, driving him on far past the point of exhaustion. “Should have…done this…ages ago…!”

“Show me!” Hilda begged, opening her eyes so she could turn her head and look back at the older man currently balls-deep in her ass and pounding away like it belonged to him. Her blue eyes were wide and innocent, pleading, her face flush and red from exertion. “Show me how much you wanted this! Please! Give it to me harder! As hard as you can! Fuck me like no one has ever fucked me before!”

So, that’s exactly what the Depot Agent did.

The subway rumbled on around the two of them, revealing only darkness in the tunnels beyond as the Depot Agent began slamming into Hilda’s ass like his life depended on it, moving so quickly the poor girl could barely keep her head on straight. Her brown hair fluttered about her wildly and her breasts began to bounce up and down beautifully despite her bra, so much so that Hilda may have begged the man to squeeze and grope them had she not been entirely focused on letting the man fuck her brains out.

“UHUHUHUHUHUHUHUH!!” Hilda moaned and whimpered loudly, unable to form coherent words anymore as the Depot Man fucked her into oblivion, stretching wide her adolescent asshole as he buried himself in her tightening bowels again and again and again. It took everything the Trainer had not to lose consciousness right then and there, the sensation of being pounded so thoroughly almost too much for her to bear. “Yuh, yuh, yes! Yes! Just like that! Fuck meeeee…!”

At this point, Hilda had all but forgotten about the deal she had made with the Depot Agent, so completely and utterly consumed was she by the ecstasy of having the man absolutely demolish her ass. She had experienced sex before, of course, but never like this, never so passionately, never in such a public place, and certainly never in her ass! The entire experience was almost too much for the young Trainer, and it wasn’t long before she was losing herself to the pleasure building up inside of her, all of it a result of the Depot Man and his fat cock buried in her bowels.

Thankfully, many minutes passed before the Depot Agent began to tire, his excitement and enthusiasm only giving way one exhaustion began to take hold, particularly as he felt himself being pushed closer and closer to the brink of his orgasm. A man could only take so much, after all, and it wasn’t every day he had the opportunity to sodomize a teenage girl, particularly one so clearly in love with the experience right from the get-go.

“F-Fuck, I’m…I’m almost there!” the Depot Agent exclaimed as his thrusts became jerky and uneven, but still fast and powerful, each one burying the entire length of his cock into Hilda’s perfect ass. “I can’t hold out! I’m gonna cum!”

“Cum inside me!” Hilda responded without a moment’s hesitation, still bucking her hips wildly and hanging on for dear life as the Depot Agent slammed into her adolescent ass. She knew what she wanted and she knew exactly where she wanted it. “Cum in my ass! I want to feel your cum in my ass, I want to feel all of it, every single drop! Please, _please_ , for the love of Arceus, cum in my tight, little ass!”

A few moments later, Hilda got her wish as the Depot Agent’s thrusts grew wild and unchecked, and he unleashed a loud and animalistic groan. Grabbing the girl’s hips and holding her as still as he could, the man buried himself to the hilt inside the young Trainer’s ass as he finally exploded inside her. Burst after burst of white hot cum gushed out of his thrusting cock, flooding Hilda’s bowels with his seed and quickly filling her to the brim.

“Mmmmm…!” Hilda whimpered happily, pleasurable shivers running up and down her spine as she felt a man cum in her ass for the very first time. She fell in love with the sensation immediately – the heat, the fullness, the dominance, even the feel of the warm liquid coating her tight bowels and flowing deeper, deeper, deeper into her young body.

Hilda didn’t know for how long she remained hanging limply from the handles above her, her knees weak and her entire body sore in the most pleasurable way possible as she came down from her own orgasm, the sensation of the Depot Agent cumming inside her providing more than enough to push her over the edge. Indeed, she may well have fallen over or even faded away into slumber had she not felt the Depot Agent slowly begin to pull his softening cock out of her tender asshole.

“Ooooh…” Hilda cooed weakly, gasping a little as sensitivity returned, forcing her to feel each and every inch of the man’s fat cock as he slid it out of her burning rectum, full as it was with his seed. When at last he had withdrawn, she felt some of the cum in her ass follow suit, and shivered a little as she felt the man’s juices dripping out of her formerly virgin anus.

“Sorry,” the Depot Agent said, blushing madly as though he has only just now returned to his senses, even as he quickly tried to put his cock away and make himself look presentable. “I, uh…may have gone a little overboard there.”

“Don’t apologize,” Hilda reassured him, weakly turning to look at the gentle man who had just finished destroying her young ass in a most _ungentle_ way. “I loved it…”

The Depot Agent smiled. “Need some help?”

“Please.”

A few minutes later, Hilda was back on her feet with her shorts back on, though it was clear she was still recovering from the brutal fucking she had endured, as evidenced by her wobbly stance and the seemingly permanent blush on her face. The girl went so far as to gently rub her ass through her shorts, clearly still tender and quite sore from the perfectly pleasurable punishment it had received. The Depot Agent simply offered her a sympathetic smile, apologetic that he may have hurt her, but clearly _not_ apologetic about _how_ he had hurt her.

“So, a deal’s a deal, right?” Hilda asked, smiling up at the Depot Agent even as she bit her lip, perhaps afraid the man might go back on his word now that he had gotten what he want. To her eternal relief, however, the man simply smiled back and nodded.

“Go on, you’ve earned it,” the Depot Agent said, moving aside and gesturing towards the door at the end of the car, the one that would lead to the girl’s fortieth battle of the day. He was surprised when, instead of simply running right past him and throwing herself into her next challenge, Hilda instead bounced over to him and quickly leaned up to give him a kiss on the cheek.

“Thanks!” she said, a blush on her cheeks and an adorable smile on her face, acting for all the world like an innocent little girl being given a gift despite everything that had occurred between them. “You’re a lifesaver!”

“Just…don’t go telling anyone about this, alright?” the Depot Agent reminded her, still a little uncertain about the whole thing, even after having received his ‘payment’ of Hilda’s perfect ass. “I _really_ don’t want to get fired.”

“My lips are sealed,” Hilda reassured him, grinning and zipping her lips closed with a finger before tossing away the key. “After all, we can’t do this again if you lose your job, can we?”

With that, the young woman was off, laughing a little as she made her way to the back of the car and on to her next challenge, leaving behind a very confused – but also very hopeful – Depot Agent to watch her go.

“Wait… _again_?”


End file.
